Following the development of Portage Park during the late-1910s and early 1920s, the neighborhood experienced a significant building boom, with much of its earliest construction occurring in the nearest vicinity to the Park, which includes this district. The park and its attractions brought large numbers of visitors to the area, and developers saw the potential in promoting single-family homeownership to Chicagoans of more limited means. This promotion of single-family homeownership countered the early-twentieth century trend that encouraged increasing residential density, a trend that characterized Chicago's urban apartments and tenements at the time, particularly for working class residents. In the 1920s, the population increased from 24,439 residents to 64,203, with most of the new residents choosing to live in a single-family dwelling, most often in Chicago bungalows. The years 1915 and 1930 represent the first and last years of construction for contributing buildings within the district.

The district embodies the characteristics of a distinctive type, period, and method of residential construction—the bungalow—and for its retention of a high degree of architectural and historic integrity. Like other early Chicago bungalow neighborhoods, Portage Park offered working class families the opportunity to own affordable, well-constructed, and thoughtfully designed homes and to build communities within a quiet residential setting. While a variety of residents, architects, and contractors contributed to the district's creation and growth, the streetscapes are strikingly cohesive, tied together with similar materials, massing, setbacks, design, and age of construction. Though in an urban environment, the Portage Park Bungalow Historic District began as and remains residential, a sharp contrast to many nineteenth and early-twentieth century Chicago communities, where residential, commercial and industrial activities frequently intersected in the built environment. The Portage Park Bungalow Historic District and other bungalow neighborhoods represent distinctive land use patterns that predate Chicago's 1923 adoption of comprehensively zoned land uses and building restrictions.

The development of the Portage Park neighborhood in the 1910s and 1920s directly related to the increasing and widespread popularity of Chicago bungalow neighborhoods built between 1907 and the early 1930s around the city center. Between 1900 and 1930 alone, Chicago's population doubled as an additional 1.5 million residents settled into the city. During this same period, the number of owner-occupied housing units in Chicago rose from 86,435 in 1900 to 261,750 in 1930. The tens of thousands of one-and-one-half story brick bungalows built in the city's outlying neighborhoods during this time stood at the forefront of the expansion of single-family homeownership. Built together, often in entire blocks, the unprecedented form of the Chicago bungalow created an entirely novel form of Chicago urbanism.

The community now known as Portage Park was once the site of an American Indian portage, used for transport from the Chicago to Des Plaines Rivers. The land in this area would flood easily when it rained, creating this shallow portage navigable by canoe. In 1816, American Indians living in the area relinquished a 20-mile wide section of land to the U.S. Federal Government, including the portion now known as Portage Park. Though originally intended to be used for a canal and military road, the government opened the land for "settlement" in 1830. After the completion of a government land survey in 1837, land sales began in earnest. In 1841, E.B. Sutherland built one of the first permanent structures along the Northwest Plank Road, now known as Milwaukee Avenue, at the spot where Milwaukee Avenue intersects with Belle Plaine Avenue. In the late 1840s and early 1850s, a private company had run this wooden plank road for a distance of 23 miles, making formerly impassable roads somewhat more navigable for new settlers. In 1845, Chester Dickinson purchased Sutherland's inn, and subsequently ran it as a post office, tavern, and interim town hall. The tavern served as a central hub of activity for Jefferson Township after it formally formed in 1873. Despite the preservation efforts of many Portage Park residents, the Dickinson Tavern was razed in 1929.

In 1851 Cook County (est. 1831) purchased 160 acres of farmland two miles west of the Dickinson Tavern for the construction of a "poor farm" and a facility for the criminally insane. The first few decades of the institution were marked by overcrowding, poor management, and threats of closure. After the Board of State Commissioners of Public Charities intervened in 1870, and over the course of the decade, facilities expanded for the growing population and service buildings like a library and pharmacy were added to the campus. By 1882, the institution and farm eventually required the construction of a single three-mile rail track running along what is now Nashville Avenue from the hospital south to the Chicago, Milwaukee, and St. Paul railroad line. Until the streetcar came to Portage Park in 1907, this rail line was the only means of transportation to the institutions. The plotting of this rail line brought more visitors and encouraged further transportation development in the area.

In the 1850s, the Chicago and Northwestern Rail road attempted to run a separate line through the newly created village, connecting an eastward line parallel to what is now Montrose Avenue with the Northwestern Railway to Mayfair station near Cicero and Wilson Avenues. A four-year delay in the ordinances permitting construction and opposition from the neighborhood residents led the railroad officials to shelve their original plans. As the story goes, neighborhood residents opposed the railroad construction so strongly that a band of 60 men took up picks and axes and tore up the tracks the railroad had already laid.

Soon after, a railroad line was constructed further east, along its present route east of Cicero Avenue. The railroad provided better access to the city center, leading to new development along the route. In 1862, a permanent town hall for Jefferson Township was constructed at the Six Corners intersection of West Irving Park Road, North Cicero and North Milwaukee Avenues—eventually the commercial center of Portage Park. Jefferson Township formally became part of Chicago when it was annexed in 1889. Even at this time, the area now known as Portage Park was mostly farm and prairie: land with a few settlements, its residents primarily of German, English, and Swedish descent.

In 1893, the Swedish Lutheran Synod appointed a committee to find a site for a new college. They chose an eighty-acre tract of prairie land in the western part of present-day Portage Park, bound by Irving Park Road, Grace Street, Central and Austin Avenues, calling it the Martin Luther Subdivision. The college building and several frame homes went up the next year, but the college eventually failed. Even so, Swedes continued to settle in this western area, building homes and a community. While many Swedes settled in the western portion of the community, the major area of settlement at the time was on the eastern side, where Germans, English, and some Swedes settled and built modest frame homes.

In the first decade of the twentieth century, both the Milwaukee Avenue and Irving Park Road rail-car lines extended into the area, causing rapid construction in the community. Development did not spread evenly throughout the area, however. Unsurprisingly, the highest concentration of newly constructed businesses and residences was located near the transportation lines.

Soon thereafter, in 1913, an independent park board formed by local residents, decided to create a park in the neighborhood. Between 1913 and 1917, the American Park Builders Company prepared the park's original plan and began its initial construction. In 1915, the park district board of commissioners and Portage Park residents fought over the board's proposed special tax of the residents to help fund the park development. In February 1916, Cook County courts invalidated the proposed tax increase over a technicality.

Despite this dispute the park's construction continued at a steady pace. A swimming lagoon opened in July 1916, but the necessities created by World War I halted construction for several years. In 1922, noted architect Clarence Hatzfield designed the prairie-style field house, now used as a cultural center for the neighborhood. In 1928, Hatzfield designed the brick gymnasium, also still in use today. Portage Park's facilities, events, and athletic offerings attracted people from the surrounding communities, making it a popular neighborhood on the northwest side. In 1922, the Fourth of July celebration held in the park brought a crowd of over 40,000 people from all over the city.

During the creation and construction of Portage Park, Chicago Public Schools constructed an elementary school at a site located within this district, surrounded by West Hutchinson Street, and North Lockwood, West Berteau, and North Long Avenues. Arthur F. Hussander, the Official Architect to the Chicago Board of Education from 1913 to 1920, designed the Portage Park Elementary School, one of over 60 new Chicago Public School buildings for which he prepared plans (an addition to the school was constructed in 1999). In its early years, a room at the school served as a meeting space for the Portage Park Women's Club, one of the many "block clubs" that developed in the neighborhood in the first quarter of the twentieth century. By 1922, the student body had swelled to such an extent that the school had to push the Women's Club out to make more room for students. Originally named after O.A. Thorp of Wicker Park, the neighborhood residents lobbied to rename the school after the community itself.

With the expanded transportation lines and construction of Portage Park and Portage Park Elementary School, real estate developers saw a lucrative opportunity for residential development in the neighborhood. The increased rates of rapid development saw prices go up to as much as $2,500 per acre, and many of the farmers who owned the land saw an opportunity to sell and move further into the country. Developers began to heavily publicize the Portage Park neighborhood and encouraged people from across the city, particularly those with limited means, to move and build residences there. They marketed the neighborhood as the perfect opportunity to own one's own home in an area that was affordable as well as elite. A typical advertisement in the Chicago Sunday Tribune from July 1922, offered readers their "opportunity to get a lot in this high class neighborhood at a very low price."

In the 1920s, residential, industrial, and commercial construction in the area quickly increased, particularly in the vicinity of the park, where the Portage Park Bungalow Historic District is located. Population in Portage Park rose drastically between 1920 and 1930, from 24,439 residents to 64,203. The 1940 Local Community Area Fact Book shows that of the 14,721 structures in the area, 9,024 (61.3%) were built between 1920 and 1929. Most of them were one- or two-story brick residential structures, the most common style being the brick bungalow. Residential construction during the early 1920s was so prevalent that the area is said to have reached residential maturity by 1924. By 1930, 80% of the dwellings in the neighborhood were single-family, and by 1939, only 35% of the residential structures were constructed of wood.

Compared to Portage Park neighborhood's overall residential building composition (80% single family, 65% masonry), this district is particularly important as a visual representation of the neighborhood's architectural and historical significance, with 94% of its contributing buildings comprised of single-family, brick Chicago bungalows.

Brick bungalows dominated the streetscape, particularly within the district. According to the 1950 Local Community Area Fact Book, "single-family brick dwellings were especially characteristic of many blocks in the vicinity of the park." The building permits issued for the bungalows and other residences in the Portage Park Bungalow Historic District reflect this rapid settlement. Permits for all 202 contributing buildings were issued between 1915 and 1930, and 186 of the 202, were issued in 1923 and 1924. According to the Cook County Property Tax Assessor's records, the majority of the brick bungalows in this district were 87 or 88 years old in 2013—putting the peak construction in the district at 1925 to 1926.

Most of the oldest bungalows in the district (built prior to 1925) are located in the 5300 and 5400 blocks of West Hutchinson Street, again demonstrating how the residential development in the district began in the area closest to the park. Most of the bungalows on West Cullom and West Pensacola went up during the district's peak construction years of 1925 and 1926. For the most part, the few contributing buildings constructed between 1926 and 1930 are located on the 5500 block of Pensacola Ave, the block in the district furthest away from Portage Park. Cost of construction for the residences in the district ranged from $3,600 to $9,000. Most bungalows in the district cost between $5,000 and $6,500, which would have been a manageable sum for working class families moving to Portage Park.

In 1920, Portage Park was largely working class—nearly 50% of its male workforce worked in manufacturing, 16% in trade, and 15% in clerical positions. Only 6% were classified as "professionals." In 1920, the overall population was predominantly Lutheran or Catholic, and white, foreign-born residents comprised 26% of the Portage Park population. Of that group, 29% were German or Austrian, 25% were Scandinavian, and 6% were Polish. In the next ten years, the German, Polish, and Italian populations increased significantly, while the Scandinavian population decreased.

District residents worked predominantly in blue-collar positions, with the majority working in building trades (carpenter, plaster man, bricklayer, etc), industry (toolmaker, laborer, tinner, repairman, etc), or other service positions (plumber, janitor, butcher, etc). Roughly 10% of the residents worked in " professional" sectors - as executives, bankers, engineers, superintendents, and even one dairy manager. Notably, of the 4 butchers listed, two were Polish, two were Austrian, and two of the three carpenters were Swedish.

Commercial development increased in the 1920s as well, reaching new heights in the 1930s. The Six Corners intersection solidified its status as the commercial center of the community in the 1930s with the LaSalle Bank and the art deco Sears and Klee's building constructed by the end of the decade. Movie palaces like the Patio Theater (1927) and the Portage Theater (1929) served as some of the community's architectural and cultural gems. Both movie palaces fell into disrepair for some time, but have since been rehabilitated and again opened to the public. Since its heyday, the Six Corners has experienced economic fluctuations, but it is currently slated for redevelopment, including a proposed street beautification project.

During the 1930s, Portage Park benefitted from the funds the Works Progress Administration allocated to the new Chicago Park District which was created in 1934 by the consolidation of 22 independent park commissions. Improvements to the park included additional plantings, stonework fountains and gateways, and a comfort station. Also during this period, the original 1916 swimming lagoon was removed and replaced with a kidney-shaped concrete pool, itself replaced by an Olympic-sized pool in 1959. Notably in 1972, Portage Park hosted the U.S. Olympic swimming trials, where Gold Medalist Mark Spitz set new world's records.

Portage Park remained a stable, residential community during the 1930s, 1940s, and 1950s, with a population hovering around 65,000 for all three decades. The 1940s saw considerable new industrial construction as well as additions to older industrial buildings, though most of this construction was confined to the northeast portion of the community.

In the 1950s, the remaining vacant lots outside of the district were filled with new residences, and new transportation routes were constructed. The Northwest (Kennedy) Expressway was completed in the late 1950s and early 1960s, cutting through the northeast corner of the Portage Park community. Also during this period, the Milwaukee "El" line (blue line) expanded to O'Hare, Kennedy Rapid Transit Terminal opened in Jefferson Park, and bus service extended through to Harlem Avenue. In the 1970s residents and Six Corners business owners successfully opposed the Crosstown Expressway, which would have run parallel to Cicero Ave.

In the second half of the twentieth century, the Portage Park population began to decline, finally dropping below 60,000 in 1980. By 1990 the population had decreased to 56,513, with residents of Polish, Italian, Irish, and German descent comprising the largest ethnic groups in the area. Despite these declines in population, the Portage Park community remained close-knit and prideful in its history and architecture. One newspaper article from 1975 referred to the bungalows as "Polish battleships" and described how the community was able to defeat the proposed Crosstown Expressway because of its united front. After several decades of declining population, the 2000 census showed the population in Portage Park had rebounded to 65,340.

Portage Park continues to remain a stable residential community in 2014. Residents in the district appear to have an appreciation of and pride in their neighborhood's history, diverse population, and cohesive architecture. That the district's bungalows maintain such high levels of historic and architectural integrity demonstrates the attention and care Portage Park residents give their homes.